MX2017008170A - Metodo para sintetizar compuestos de carbonilo opticamente activos. - Google Patents
Metodo para sintetizar compuestos de carbonilo opticamente activos.Info
- Publication number
- MX2017008170A MX2017008170A MX2017008170A MX2017008170A MX2017008170A MX 2017008170 A MX2017008170 A MX 2017008170A MX 2017008170 A MX2017008170 A MX 2017008170A MX 2017008170 A MX2017008170 A MX 2017008170A MX 2017008170 A MX2017008170 A MX 2017008170A
- Authority
- MX
- Mexico
- Prior art keywords
- optically active
- aryl
- carbonyl compound
- carbonil
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229910052723 transition metal Inorganic materials 0.000 abstract 2
- 150000003624 transition metals Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 230000001566 pro-viral effect Effects 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención se refiere a un proceso para la preparación de un compuesto de carbonilo ópticamente activo por hidrogenación asimétrica de un compuesto de carbonilo a,ß-no saturado proquiral con hidrógeno en presencia de al menos un catalizador de metal de transición ópticamente activo que es soluble en la mezcla de reacción y que tiene rodio como metal de transición catalíticamente activo y un ligando de bisfosfina bidentado quiral, donde la mezcla de reacción durante la hidrogenación del compuesto de carbonilo a,ß-no saturado proquiral comprende adicionalmente al menos un compuesto de la fórmula general (I): (ver Fórmula) donde R1, R2: son idénticos o diferentes y son arilo C6 a C10 que no está sustituido o lleva uno o más, por ejemplo 1, 2, 3, 4 o 5, sustituyentes que se seleccionan de alquilo C1 a C6, cicloalquilo C3 a C6, arilo C6 a C10, alcoxi C1 a C6 y amino; Z es un grupo CHR3R4 o arilo que no está sustituido o lleva uno o más, por ejemplo 1, 2, 3, 4 o 5, sustituyentes que se seleccionan de alquilo C1 a C6, cicloalquilo C3 a C6, arilo C6 a C10, alcoxi C1 a C6 y amino, donde R3 y R4 son como se definen en las reivindicaciones y la descripción.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14199410 | 2014-12-19 | ||
| PCT/EP2015/080392 WO2016097242A1 (de) | 2014-12-19 | 2015-12-18 | Verfahren zur herstellung optisch aktiver carbonylverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2017008170A true MX2017008170A (es) | 2017-09-18 |
| MX375969B MX375969B (es) | 2025-03-06 |
Family
ID=52231936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2017008170A MX375969B (es) | 2014-12-19 | 2015-12-18 | Metodo para sintetizar compuestos de carbonilo opticamente activos. |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US9975837B2 (es) |
| EP (2) | EP3489213B1 (es) |
| JP (1) | JP6702974B2 (es) |
| CN (1) | CN107250091B (es) |
| ES (2) | ES2727384T3 (es) |
| MX (1) | MX375969B (es) |
| WO (1) | WO2016097242A1 (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107735392B (zh) | 2015-05-04 | 2021-12-03 | 巴斯夫欧洲公司 | 制备甜瓜醛的方法 |
| ES2835060T3 (es) | 2015-10-12 | 2021-06-21 | Basf Se | Procedimiento de hidroformilación para preparar derivados de hexano 1,6-disustituidos |
| ES2899827T3 (es) | 2015-12-08 | 2022-03-14 | Basf Se | Material zeolítico que contiene estaño y que tiene una estructura de marco BEA |
| ES2844182T3 (es) | 2016-06-07 | 2021-07-21 | Basf Se | Procedimiento para la preparación de alcoholes con insaturación en posición 2,3 |
| MY191494A (en) | 2016-06-29 | 2022-06-28 | Basf Se | Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols in the presence of a liquid phase |
| ES2857957T3 (es) | 2016-10-06 | 2021-09-29 | Basf Se | Procedimiento de enriquecimiento de enantiómeros a partir de una mezcla de enantiómeros |
| WO2019121012A1 (en) * | 2017-12-21 | 2019-06-27 | Basf Se | Process for the preparation of alpha, beta unsaturated aldehydes by oxidation of alcohols in the presence of a liquid phase |
| EP3847151B1 (de) * | 2018-09-05 | 2022-11-09 | Basf Se | Kontinuierliche herstellung einer optisch aktiven carbonylverbindung durch asymmetrische hydrierung |
| CN112770834B (zh) * | 2018-09-05 | 2023-07-21 | 巴斯夫欧洲公司 | 进行气/液两相高压反应的方法 |
| ES2933963T3 (es) | 2018-09-05 | 2023-02-15 | Basf Se | Reactor para llevar a cabo una reacción entre dos fluidos inmiscibles de diferentes densidades |
| ES2934908T3 (es) | 2018-09-05 | 2023-02-27 | Basf Se | Reactor para llevar a cabo una reacción bifásica de gas/líquido de alta presión con un medio espumante |
| US20220242807A1 (en) * | 2019-05-27 | 2022-08-04 | Dsm Ip Assets B.V. | Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound |
| CN111056932A (zh) * | 2019-12-09 | 2020-04-24 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法 |
| WO2021114021A1 (zh) | 2019-12-09 | 2021-06-17 | 万华化学集团股份有限公司 | 一种光学活性的香茅醛的制备方法 |
| CN110872217A (zh) * | 2019-12-09 | 2020-03-10 | 万华化学集团股份有限公司 | 一种光学活性的香茅醛的制备方法 |
| CN111004102B (zh) * | 2019-12-23 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂 |
| CN111056933B (zh) * | 2019-12-24 | 2022-11-08 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂体系 |
| CN111792986B (zh) * | 2020-07-22 | 2022-09-20 | 万华化学集团股份有限公司 | 一种制备r-香茅醛的方法 |
| CN112142583B (zh) * | 2020-10-26 | 2022-07-26 | 万华化学集团股份有限公司 | 一种香叶醛制备橙花醛的方法 |
| CN113527367B (zh) * | 2021-07-14 | 2022-08-02 | 南开沧州渤海新区绿色化工研究有限公司 | 一种含四（3,5-二三氟甲基苯基）硼阴离子的手性双膦配体铑络合物和制备方法及应用 |
| WO2025011972A1 (en) | 2023-07-07 | 2025-01-16 | Basf Se | Photoisomerization of geranial and neral |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123465A (en) * | 1975-10-16 | 1978-10-31 | Hoffmann-La Roche Inc. | Chiral tertiary phosphines |
| JPS5278812A (en) | 1975-12-26 | 1977-07-02 | Nikki Chem Co Ltd | Selective production method of saturated aldehyde |
| FR2396735A1 (fr) | 1977-07-04 | 1979-02-02 | Rhone Poulenc Ind | Procede de preparation de citronellal optiquement actif |
| DE19854637A1 (de) | 1998-11-26 | 2000-05-31 | Basf Ag | Reaktor zur kontinuierlichen Durchführung von Gas-Flüssig-, Flüssig-Flüssig- oder Gas-Flüssig-Fest-Reaktionen |
| JP4676617B2 (ja) | 2001-01-18 | 2011-04-27 | 高砂香料工業株式会社 | イソプレゴールの製造方法 |
| DE102004049631A1 (de) * | 2004-10-11 | 2006-04-20 | Basf Ag | Verfahren zur Herstellung optisch aktiver Carbonylverbindungen |
| DE102004057277A1 (de) * | 2004-11-26 | 2006-06-01 | Basf Ag | Verfahren zur Herstellung von Menthol |
| ES2636840T3 (es) * | 2007-04-25 | 2017-10-09 | Basf Se | Procedimiento para la preparación de compuestos carbonílicos ópticamente activos |
| AR070176A1 (es) * | 2008-01-17 | 2010-03-17 | Novartis Ag | Procesos de sintesis de inhibidores de nep, compuestos intermediarios y uso de los mismos en la sintesis |
| JP5711209B2 (ja) * | 2010-03-04 | 2015-04-30 | 高砂香料工業株式会社 | 均一系不斉水素化触媒 |
-
2015
- 2015-12-18 EP EP18206833.8A patent/EP3489213B1/de active Active
- 2015-12-18 ES ES15817247T patent/ES2727384T3/es active Active
- 2015-12-18 MX MX2017008170A patent/MX375969B/es active IP Right Grant
- 2015-12-18 EP EP15817247.8A patent/EP3233778B1/de active Active
- 2015-12-18 US US15/536,524 patent/US9975837B2/en active Active
- 2015-12-18 WO PCT/EP2015/080392 patent/WO2016097242A1/de not_active Ceased
- 2015-12-18 ES ES18206833T patent/ES2883557T3/es active Active
- 2015-12-18 CN CN201580076501.0A patent/CN107250091B/zh active Active
- 2015-12-18 JP JP2017532651A patent/JP6702974B2/ja active Active
-
2018
- 2018-04-27 US US15/964,400 patent/US10301244B2/en not_active Ceased
-
2019
- 2019-07-25 US US16/521,935 patent/USRE49036E1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN107250091B (zh) | 2021-05-04 |
| JP2017537965A (ja) | 2017-12-21 |
| EP3489213A1 (de) | 2019-05-29 |
| US10301244B2 (en) | 2019-05-28 |
| EP3489213B1 (de) | 2021-04-28 |
| US20180244598A1 (en) | 2018-08-30 |
| CN107250091A (zh) | 2017-10-13 |
| EP3233778B1 (de) | 2019-02-20 |
| MX375969B (es) | 2025-03-06 |
| USRE49036E1 (en) | 2022-04-19 |
| US20180057437A1 (en) | 2018-03-01 |
| WO2016097242A1 (de) | 2016-06-23 |
| JP6702974B2 (ja) | 2020-06-03 |
| EP3233778A1 (de) | 2017-10-25 |
| US9975837B2 (en) | 2018-05-22 |
| ES2883557T3 (es) | 2021-12-09 |
| ES2727384T3 (es) | 2019-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |